Sodium Hydroxide → 2-[3-(3-Nitrophenyl)isoxazol-5-ylmethyl]-1,2,3,4-tetrahydroisoquinoline

HRID 914985Notes

Reaction equation

HRID 914985 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]#[N+:9][O-:10])([O-:4])=[O:3].[CH2:14]([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)[C:15]#[CH:16].[OH-].[Na+]>C1(C)C=CC=CC=1>[N+:2]([C:5]1[CH:6]=[C:7]([C:8]2[CH:16]=[C:15]([CH2:14][N:17]3[CH2:26][CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)[O:10][N:9]=2)[CH:11]=[CH:12][CH:13]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 143412942-(Prop-2-yn-1-yl)-1,2,3,4-tetrahydroisoquinolineHCID 865943233-Nitrobenzonitrile oxide hydrogen chloride

Product 1

HCID 589580412-[3-(3-Nitrophenyl)isoxazol-5-ylmethyl]-1,2,3,4-tetrahydroisoquinolineYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 80 (0.2 g, 1.0 mmol) and 81 (0.2 g, 1.17 mmol) in toluene (5 mL) was heated at reflux for 4 hours. The reaction was cooled and mixed with 0.5 N NaOH (5 mL), then extracted with ethyl acetate (2×10 mL). The organic material was combined, dried (K2CO3) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient elution, hexane to 3:1 hexane/ethyl acetate) to give 82 (228 mg, 68%) as a yellow oil.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate (2×10 mL)
  4. dry with materialdried (K2CO3)
  5. concentrationthen concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (SiO2, gradient elution, hexane to 3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c5894c428c454dc5a5c02a62221d3ea4
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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